2,7-diphenyl[1]benzoselenopheno[3,2-b][1]benzoselenophene as a stable organic semiconductor for a high-performance field-effect transistor

Kazuo Takimiya; Yoshihito Kunugi; Yasushi Konda; Hideaki Ebata; Yuta Toyoshima; Tetsuo Otsubo

doi:10.1021/ja057641k

2,7-diphenyl[1]benzoselenopheno[3,2-b][1]benzoselenophene as a stable organic semiconductor for a high-performance field-effect transistor

J Am Chem Soc. 2006 Mar 8;128(9):3044-50. doi: 10.1021/ja057641k.

Authors

Kazuo Takimiya¹, Yoshihito Kunugi, Yasushi Konda, Hideaki Ebata, Yuta Toyoshima, Tetsuo Otsubo

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima 739-8527, Japan. ktakimi@hiroshima-u.ac.jp

PMID: 16506786
DOI: 10.1021/ja057641k

Abstract

[1]Benzoselenopheno[3,2-b][1]benzoselenophene (BSBS) and its 2,7-diphenyl derivative (DPh-BSBS) were readily synthesized from diphenylacetylene and bis(biphenyl-4-yl)acetylene, respectively, with a newly developed straightforward selenocyclization protocol. In contrast to the parent BSBS that has poor film-forming properties, the diphenyl derivative DPh-BSBS formed a good thin film on the Si/SiO(2) substrate by vapor deposition. X-ray diffraction examination revealed that this film consists of highly ordered molecules that are nearly perpendicular to the substrate, making it suitable for use in the fabrication of organic field-effect transistors (OFETs). When fabricated at different substrate temperatures (room temperature, 60 degrees C, and 100 degrees C) in a "top-contact" configuration, all the DPh-BSBS-based OFET devices exhibited excellent p-channel field-effect properties with hole mobilities >0.1 cm(2) V(-1) s(-1) and current on/off ratios of approximately 10(6). This high performance was essentially maintained over 3000 continuous scans between V(g) = +20 and -100 V and reproduced even after storage under ambient laboratory conditions for at least one year.